Wrinkle drying oil siccative



United States {O 2,744,832 WRINKLE DRYING OIL SICCATIVE No Drawing. Application July 17, 1952, Serial No. 299,508

2 Claims. (Cl. 106-264) This invention appertains to coating compositions which dry to a wrinkle finish when applied on asurface and allowed to dry under normal atmospheric conditions or through the application of heat and/or forced air.

Briefly the invention consists in the provision of a coating composition of the character described comprising as a fatty oil vehicle, or drying oil accelerator, the mixed giycerides of conjugated keto polyethenoid C18 acids having two active methylene groups adjacent to the carbonyl group in the molecular structure (one of which has been converted to a C=O group) and the glycerides of isomeric eleostearic acids. Henceforth, in this test, such mixtures of polyethenoid keto Cm acids and isomeric eleostearic acids will be referred to as the subject acids.

It is an object of this invention to provide a novel drying oil vehicle for coating compositions by the incorporation of. substantial amounts of glycerides of the subject acids thereinto as an addition agent or during the manufacture thereof.

Another object of this invention is to provide a drying oil blend or vehicle consisting of the glycerides of polyethenoid C18 and isomeric eleostearic fatty acids of the character described which may be incorporated into a drying oil coating composition to produce a product having accelerated drying properties.

Wrinkle drying compositions have been compounded heretofore utilizing vegetable drying oils such as, Chinawood oil or oiticica oil, containing conjugated double bond glycerides, or such as, linseed oil, containing acid glyceride with unconjugated double bonds which are capable of being isomerized to conjugated positions by heat treating. See, for example, The Science of Wrinkle Finishing by W. A. Waldie (-1949), Appendix A. Further, it has been disclosed in a publication Proceedings of Indian Academy of Science, in an article by S. V. Puntambekar, that the fatty oil from the seeds of Mallotus philippinensis Muel-Arg probably containing glycerides of fatty acids such as may be represented by the following:

isomeric keto linoleic acid (b) CHM) Ha) z-C H=O HCH=C H-C H=C H-(CH:)1COOH eleostearie acid 2-(a) CHr-(C Hs):-C H=O H-C H=C HCH=CH(l3 --(OH|)a-GOOH keto eleostearic acid (b) C H;(C Ha) 9-CH=C H-C H=C HCH=C H-C Hr-C O OH isomeric elestearie acid The present invention is based on the utilization of a mixture of glycerides of the subject acids as a wrinkle drying mixture or fatty oil siccative or as a smooth finish drying accelerator mixture or concentrate.

The mixture of glycerides of the fatty acids and wherein at least one is a keto polyethenoid acid appears to ice provide a synergistic catalytic action inasmuch as the fatty glycerides alone do not show the improved drying results. Thus, the drying oil vehicle of this invention comprises a combination of the glycerides of keto polyethenoid fatty acids and the glycerides of eleostearic or isomeric eleostearic acids to produce the desired improved drying results.

in accordance with the present invention, it is possible to produce wrinkle drying compositions which air dry in a' shorter time than tung oil or (China-wood oil) compositions, the invention providing a composition having improved drying characteristics over that of like compositions containing tung oil.

Preferably the percentages of the described mixture of the subject fatty acid glycerides constitute upwards of 60% and, generally, or more of the fatty oil vehicle for producing wrinkle drying compositions, or may be introduced in lesser amounts for the production of nonwrinkling smooth drying finishes.

ln practising the invention a blend of the fatty acid glycerides is perferably made up as by suitably mixing the acid glycerides'together in the desired proportions, or by incorporating the glycerides with a small amount of fatty oil, for example employing a vegetable drying oil such as linseed oil, tung oil or the like, to form a homogeneous mixture. A suitable composition may consist of a mixture of the glycerides of the fatty acids of 1(a) and 1(b) or 2(a) and 2(b) or any combination of two or more of these wherein at least one of the fatty glycerides is a keto polythenoid Cm acid glyceride. It is also contemplated that a suitable siccative may comprise a mixture of a keto polythenoid C18 glyceride blended with one or more of the free C13 fatty acids. That is where only the keto C18 fatty acid of the siccative product is in the form of a glyceride.

Where it is desired, in some instances, utilization may be made of a suitable mixture of the subject acids when a sufiicient amount of polyalcohol materials are present in the mixture and are reacted with the subject acids to produce glycerides thereof.

Among the various oils suitable for blending with the glycerides of the subject acids are linseed oil, blown linseed oil, soya oil, castor oil, as well as fish and marine mammal oils, and others such as used commonly to cheapen or extend coating compositions. The extending oil may be present in amounts constituting 0-100% of the total blend of oils, depending upon the rate of drying desired. The mixture of oils is achieved by cold blending. The addition of suitable oil soluble driers, for example metal naphthenates or phthalates, may be made as desired to enhance the drying properties.

The subject acid glycerides or blends of same with drying or semi-drying oils may also be compounded with suitable resins, natural and synthetic, as are compatible. Among resins which may be used are kauri, congo, damar, pontianak, manila, phenol-formaldehyde-rosin, rosin modified maleic esters, glycerol-phthalic esters and others. The coating compositions containing these resins may be either air dried or baked to produce a dry, smooth or wrinkled, flexible, water resistant film. Air drying is especially feasible where large amounts of the subject acid glycerides are present.

A typical example of wrinkling oil blends is:

Example I Parts by weight Fatty oil 20 to 40 Subject acid glycerides 1 to 60 Mixed glycerides of conjugated e. g. keto polyethenoid Cm acids and isomeric eleostearic acids.

As the fatty oil constituent there may be used driving or semi-drying oil which is compatible with subject acid glycerides. Bodied linseed oil, tung oil, soya oil, and oiticia oil are specific examples of fatty oils whichmay be used.

As exemplary of a suitable wrinkle finish varnish. which may be employed, the following formulae are given:

Example 11 Parts by weight Resin. (Cumar, Congo, Amberol F-7) 100 Subject acid glycerides 100 Toluol 150 Naphtha (V. M. P.) 50 Cobalt Naphthaenate (6% Co) 1 Lead Naphthenate (24% Pb) 2 Antiskinning (,polyhydroxyl phenols e. g. beta naphthol, eugenol) 0.1

Example III Parts by weight Amberol F-7 100 Subject acid Glycerides 160 Xylol 140 Naphtha. v. M. P) 80 Cobalt Naphthenate (6% Co) 1.5 Lead Naphthenate (24% Pb) 3.0 Antiskinning (as in Example II) 0.1

As an example of a suitable non-wrinkling finish varnish which may be employed, the following formula is given:

Example IV Parts by weight Amberol F-7 100 Subject acid glycerides 32 Soya oil 128 Toluol 150 Naphtha (V. M. P.) 110 Cobalt Naphthenate (6% Co) 1.5 Lead Naphthenate (24% Pb) 1 Antiskinru'ng (as in Example ll) 0.2

In preparing the resinous-fatty acid glycerides of Examples II, III, and IV, the resins are first dissolved in the aromatic thinner; this is followed by addition, in turn, of the aliphatic thinner, the oil component, the an 4 tiskinning agent and the driers, the latter two items being optional.

Where it is desired to provide a highly flexible fast drying film incorporation of the subject acids in glycerol phthalate or other alkyd type formulations can be accomplished by careful reaction techniques so as to prevent premature polymerization. Further, where enamels or colored films are desired, suitable pigments may be included in the vehicles of the subject fatty acids, or their glycerides, by grinding the pigment with a portion of the vehicles, per usual pigmentation methods.

The coating composition may be applied by brushing, spraying, dipping, or the like. To this end, it is only necessary that the coating adhere to undercoating or the uncoated surface.

it will be understood that it is desired to comprehend within this invention such modifications as come within the scope of this invention as hereinbefore described, and as set out more particularly in" the appended claims.

Having set forth fully my invention, what I claim as new and desire to secure by Letters Patent is:

l. A wrinkle drying fatty oil siceative consisting of a mixture of fatty drying oil and conjugated mixed glycerides of keto polyethenoid C13 fatty acids and isomeric eleostearic acids, the mixed glycerides constituting about 70% by Weight of the sicc'ative.

2. A wrinkle drying fatty oil siccative consisting of a mixture of fatty drying oil and conjugated mixed glycerides of keto polyethenoid C18 fatty acids and isomeric eleostearic acids, the mixed glycerides constituting about to about by weight of the siccative.

References Cited in the file of this patent UNITED STATES PATENTS 2,268,022 Drummond Dec. 30, 1941 2,381,653 Drummond Aug. 7, 1945 2,455,540 Waldie Dec. 7, 1948 2,517,838 Carleton Aug. 8,1950 2,589,314 Wood et al. Mar. 18, 1952 2,623,888 Nichols Dec. 30, 1952 

1. A WRINKLE DRYING FATTY OIL SICCATIVE CONSISTING OF A MIXTURE OF FATTY DRYING OIL AND CONJUGATED MIXED GLYCERIDES OF KETO POLYETHENOIL C18 FATTY ACIDS AND ISOMERIC ELEOSTEARIC ACIDS, THE MIXED GLYCERIDES CONSTITUTING ABOUT 70% BY WEIGHT OF THE SICCATIVE. 